[NH2:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[NH:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#[N:17].[C:21](Cl)(=[O:26])[CH2:22][C:23](Cl)=[O:24]>O1CCCC1>[C:16]([C:15]1[CH:14]=[C:13]([N:12]2[C:23](=[O:24])[CH2:22][C:21](=[O:26])[NH:1][C:2]3[C:11]4[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=4[CH:5]=[CH:4][C:3]2=3)[CH:20]=[CH:19][CH:18]=1)#[N:17]To an anhydrous tetrahydrofuran (30 mL) solution of 3-(1-amino-5,6,7,8-tetrahydronaphthalen-2-ylamino)benzonitrile (747 mg, 2.84 mmol) was added an anhydrous tetrahydrofuran (5 mL) solution of malonyl chloride (276 μL, 2.84 mmol) under cooling in ice-bath. The mixture was stirred for 30 minutes under cooling in ice-bath, and for 2 hours at room temperature. To the mixture was added purified water. The mixture was extracted with ethyl acetate, washed with purified water, and dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=1/1) to give the titled compound as white powder (333 mg, yield 35%).
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